First of all, thanks to everyone who contributed to this post thus far. Today I took a brand new (from HomeDepot) wink, rooted it via the NAND flash method, then followed the update procedure exactly (on page 1), and now I have a fully updated, rooted wink! Just to verify the versions, here ya go:

-----BEGIN PUBLIC KEY-----MIIBIjANBgkqhkiG9w0BAQEFAAOCAQ8AMIIBCgKCAQEAumZE0qsNgtTQNCOhqx8++3DQG33HIvgqdPJ9qa4A9rdtuTADJ3FUnO53+EQYFuZaZ8RK76DQddtqCUzRyra7JI9RTXxYX4VWxTMEfKMoi2R79BFPOXg61Q3ZCZ4RP2gz1Mkso59ULNziLmeSQwSKudeTSmkcLUql9Ygtx8iro+JiFBr6wwyLFm+KblkRvk7aYjctdJvGOGUfoYKyKQJz5mXQiHoCqpkqdNL436paQjsxIdcEqu+iRl8n2BIgDqxHg1ZTdiNe6NIyohkaG97rRfzv2LZQ9zgfdQfGArwc9B+AGyKFJ4FgW0SdCmZSNrpqoEVCS1Xuw8QLe6oraMuCMwIDAQAB-----END PUBLIC KEY-----

So... I gave up on waiting for someone else to figure out how to do the upgrade and figured that I would give up root and tell the app to do it. I removed the blocks from /etc/hosts and told the app to upgrade. The hub flashed green for a while then went to a state of yellow and sat there. I was still logged in and it seemed that some of the upgrade process might have run but it did not reboot. I figured that might be because I had already set things up to prevent the reboot, so i did it by hand. The hub rebooted and I got back into it and could see that it had mounted the upgrade partition, then it rebooted on its own again and was up and running 2.66 and I could still ssh in. Happy Days!

I went through the process on the first page of the thread to return the hub to the state where ssh will still be enabled on the next upgrade but the reboot must be done by hand. Before I went through this process the app showed 2.68 as being available but it is not showing now, it may show up again in a day or two.

So long story short, it looks like if your hub is rooted and both the main partition and the upgrade partition are set up to still allow ssh, you "should" be able to let the app do the upgrade and still have root on the hub afterward. At least that was the case going from 2.49 to 2.66.

What I meant by going through the process is that i mounted the update partition and commented out things to make sure that I would be able to ssh in after it booted to that partition.

I did the update to the latest today and was able to log in during the process and had to reboot the hub manually after each step. Unfortunately after the final reboot I could no longer ssh into the box. It looks like ssh is still enabled but my key didn't work so either i missed a step or they've taken measures on the update to block jailbreaking it. Not really a big deal, I never used root access for anything and now i can just tell it to update and forget about it.

Today i updated my hub to 3.4.4 and it hung during the process. Thinking that maybe the upgrade partition was still rooted and blocking the reboot, i tried and was able to log into the hub. I was then able to root the new partition and restore access by adding my ssh keys and disabling dropbear (now in /etc/init.d). After I rebooted, the hub came up running 3.4.4.xxx and I had regained root access. I'm a happy camper